Photochromic Lactone-Fused Phenanthropyrans with Broad Absorption and Rapid Color Change

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  • Vânia Graça
    Centro de Química - Vila Real, Universidade de Trás-os-Montes e Alto Douro, 5000-801 Vila Real , Portugal
  • Céu M Sousa
    Centro de Química - Vila Real, Universidade de Trás-os-Montes e Alto Douro, 5000-801 Vila Real , Portugal
  • Paulo J Coelho
    Centro de Química - Vila Real, Universidade de Trás-os-Montes e Alto Douro, 5000-801 Vila Real , Portugal

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<jats:title>Abstract</jats:title> <jats:p>New lactone-fused phenanthrol[1,2-b]pyrans were successfully synthesized in 4 steps from naphthaldehydes using, as the key step, the acid-catalyzed cascade condensation of methyl 1-hydroxyphenanthrene-3-carboxylates with diarylbut-2-yne-1,4-diols, which forms the pyran and lactone rings. After exposing CHCl3 solutions of these polyaromatic compounds to UV or sunlight, at room temperature, the color changes vividly from slightly yellow to deep red/brown in a matter of seconds, and fades spontaneously, in the dark, within 1.5 min.</jats:p>

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